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seneciphylline
senecionan-11,16-dione, 13,19-didehydro-12-hydroxy- (9CI)

Supplier Sponsors

CAS Number: 480-81-9Picture of molecule3D/inchi
FDA UNII: 0ZYZ9L5454
MDL:MFCD00221722
XlogP3-AA:0.70 (est)
Molecular Weight:333.38431000
Formula:C18 H23 N O5
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Appearance:white powder (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 217.50 °C. @ 760.00 mm Hg
Boiling Point: 577.70 °C. @ 760.00 mm Hg (est)
Flash Point: 578.00 °F. TCC ( 303.20 °C. ) (est)
logP (o/w): 0.810 (est)
Soluble in:
 water, 1e+006 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Seneciphylline >98%
Odor: characteristic
Use: Seneciphylline, a natural pyrrolizidine alkaloid isolated from the herbs of Senecio scandens,
ExtraSynthese
For experimental / research use only.
Seneciphylline (GC) ≥90%
Santa Cruz Biotechnology
For experimental / research use only.
Seneciphylline
Sigma-Aldrich
For experimental / research use only.
Seneciphylline
analytical standard
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intravenous-mouse LD50 90 mg/kg
BLOOD: "LYMPHOMA, INCLUDING HODGKIN'S DISEASE" LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Research Today. Vol. 5, Pg. 53, 1949.

oral-mouse LD50 150 mg/kg
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 24(11), Pg. 64, 1980.

intraperitoneal-rat LD50 77 mg/kg
Pharmazie. Vol. 49, Pg. 934, 1994.

intravenous-rat LD50 80 mg/kg
LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA BLOOD: "LYMPHOMA, INCLUDING HODGKIN'S DISEASE"
Research Today. Vol. 5, Pg. 53, 1949.

oral-rat LD50 77 mg/kg
Toxicology Letters. Vol. 15, Pg. 19, 1983.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for seneciphylline usage levels up to:
 not for fragrance use.
 
Recommendation for seneciphylline flavor usage levels up to:
 not for flavor use.
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Dietary exposure assessment to pyrrolizidine alkaloids in the European population
View page or View pdf

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5281750
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
Chemidplus:0000480819
EPA/NOAA CAMEO:hazardous materials
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5281750
Pubchem (sid):134974514
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C10391
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 senecio vulgaris
Search Trop Picture
 
Synonyms:
13,19-didehydro-12-hydroxysenecionan-11,16-dione
trans-15-ethylidene-12beta-hydroxy-12alpha-methyl-13-methylenesenec-1-enine
 jacodine
 seneci(o)phylline
 senecionan-11,16-dione, 13,19-didehydro-12-hydroxy- (9CI)
 seneciphyllin
 seniciphylline
 

Articles:

PubMed:UPLC-MS/MS method for determination of selected pyrrolizidine alkaloids in feed.
PubMed:Toxicity of pyrrolizidine alkaloids to Spodoptera exigua using insect cell lines and injection bioassays.
PubMed:Mass-spectrometry-directed analysis and purification of pyrrolizidine alkaloid cis/trans isomers in Gynura japonica.
PubMed:[Determination of five pyrrolizidine alkaloids in honey by liquid chromatography-tandem mass spectrometry].
PubMed:Assessment of pyrrolizidine alkaloid-induced toxicity in an in vitro screening model.
PubMed:Pyrrolizidine alkaloids: their occurrence in Spanish honey collected from purple viper's bugloss (Echium spp.).
PubMed:Analysis of pyrrolizidine alkaloids and evaluation of some biological activities of Algerian Senecio delphinifolius (Asteraceae).
PubMed:In vitro 5-LOX inhibitory and antioxidant activities of extracts and compounds from the aerial parts of Lopholaena coriifolia (Sond.) E. Phillips & C.A. Sm.
PubMed:Definitive diagnosis of hepatic sinusoidal obstruction syndrome induced by pyrrolizidine alkaloids.
PubMed:Authentication of Senecio scandens and S. vulgaris based on the comprehensive secondary metabolic patterns gained by UPLC-DAD/ESI-MS.
PubMed:Hepatic sinusoidal obstruction syndrome associated with consumption of Gynura segetum.
PubMed:Pyrrolizidine alkaloids in pollen and pollen products.
PubMed:Simultaneous characterization of pyrrolizidine alkaloids and N-oxides in Gynura segetum by liquid chromatography/ion trap mass spectrometry.
PubMed:Identification of five hepatotoxic pyrrolizidine alkaloids in a commonly used traditional Chinese medicinal herb, Herba Senecionis scandentis (Qianliguang).
PubMed:Determination of pyrrolizidine alkaloids in senecio species by liquid chromatography/thermospray-mass spectrometry and liquid chromatography/nuclear magnetic resonance spectroscopy.
PubMed:Pyrrolizidine alkaloid level in Senecio bicolor (Wilid.) Tod, ssp. cineraria (DC.) from middle Europe.
PubMed:Dynamic pH junction-sweeping capillary electrophoresis for online preconcentration of toxic pyrrolizidine alkaloids in Chinese herbal medicine.
PubMed:Separation and determination of toxic pyrrolizidine alkaloids in traditional Chinese herbal medicines by micellar electrokinetic chromatography with organic modifier.
PubMed:Preventive activity of pyrrolizidine alkaloids from Seneciobrasiliensis (Asteraceae) on gastric and duodenal induced ulcer on mice and rats.
PubMed:Evaporative light scattering detection of pyrrolizidine alkaloids.
PubMed:Loss of gustatory responses to pyrrolizidine alkaloids after their extensive ingestion in the polyphagous caterpillar Estigmene acrea.
PubMed:Experience influences gustatory responsiveness to pyrrolizidine alkaloids in the polyphagous caterpillar, Estigmene acrea.
PubMed:Toxicity of Senecio vernalis to laying hens and evaluation of residues in eggs.
PubMed:Metabolism of pyrrolizidine alkaloids by Peptostreptococcus heliotrinreducens and a mixed culture derived from ovine ruminal fluid.
PubMed:A highly sensitive taste receptor cell for pyrrolizidine alkaloids in the lateral galeal sensillum of a polyphagous caterpillar, Estigmene acraea.
PubMed:Toxic pyrrolyzidine alkaloids from three mongolian plants. a possible risk for cattle poisoning.
PubMed:Alkaloids from Senecio aquaticus.
PubMed:Pyrrolizidine alkaloids from Senecio lorenthii.
PubMed:Interplant alkaloid variation and Senecio vernalis toxicity in cattle.
PubMed:The relationship between reactivity of metabolites of pyrrolizidine alkaloids and extrahepatic toxicity.
PubMed:Generation and characterization of monoclonal antibodies against the pyrrolizidine alkaloid retrorsine.
PubMed:Determination of pyrrolizidine alkaloids in honey from selected sites by solid phase extraction and HPLC-MS.
PubMed:Transfer of 14C-seneciphylline into sheep milk following multiple oral intakes.
PubMed:A competitive enzyme immunoassay for the pyrrolizidine alkaloids of the senecionine type.
PubMed:Preparative separation of pyrrolizidine alkaloids by high-speed counter-current chromatography.
PubMed:The comparative metabolism of the four pyrrolizidine alkaloids, seneciphylline, retrorsine, monocrotaline, and trichodesmine in the isolated, perfused rat liver.
PubMed:Reversible hepatic veno-occlusive disease in an infant after consumption of pyrrolizidine-containing herbal tea.
PubMed:Hydrolysis rates of pyrrolizidine alkaloids derived from Senecio jacobaea.
PubMed:Structural influences on pyrrolizidine alkaloid-induced cytopathology.
PubMed:Pyrrolizidine alkaloids from Senecio leucanthemifolius and Senecio rodriguezii.
PubMed:Hydrolysis of pyrrolizidine alkaloids by guinea pig hepatic carboxylesterases.
PubMed:Mutagenicity of pyrrolizidine alkaloids in the Salmonella typhimurium/mammalian microsome system.
PubMed:Pyrrolizidine alkaloids from Melampyrum pratense.
PubMed:DNA cross-linking in mammalian cells by pyrrolizidine alkaloids: structure-activity relationships.
PubMed:[Studies on the alkaloids of Gynura segetum (Lour.) Merr].
PubMed:Pyrrolizidine alkaloids in Senecio vulgaris L. growing in Iceland.
PubMed:Influence of inhibition of the metabolic activation on the mutagenicity of some nitrosamines, triazenes, hydrazines and seniciphylline in Drosophila melanogaster.
PubMed:Microsomal metabolism of pyrrolizidine alkaloids: N-oxidation of seneciphylline and senecionine.
PubMed:Microsomal metabolism of pyrrolizidine alkaloids from Senecio jacobaea. Isolation and quantification of 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine and N-oxides by high performance liquid chromatography.
PubMed:Genotoxicity and cytotoxicity of selected pyrrolizidine alkaloids, a possible alkenal metabolite of the alkaloids, and related alkenals.
PubMed:Method for determination of pyrrolizidine alkaloids and their metabolites by high-performance liquid chromatography.
PubMed:Genotoxicity of a variety of pyrrolizidine alkaloids in the hepatocyte primary culture-DNA repair test using rat, mouse, and hamster hepatocytes.
PubMed:In vivo covalent binding of retronecine-labelled [3H]seneciphylline and [3H]senecionine to DNA of rat liver, lung and kidney.
PubMed:Induction of SCEs by some pyrrolizidine alkaloids in V79 Chinese hamster cells co-cultured with chick embryo hepatocytes.
PubMed:Effect of seneciphylline and senecionine on hepatic drug metabolizing enzymes in rats.
PubMed:Mutagenic activity of the pyrrolizidine alkaloids seneciphylline and senkirkine in Drosophila and their transfer into rat milk.
PubMed:Transfer of [3H]pyrrolizidine alkaloids from Senecio vulgaris L. and metabolites into rat milk and tissues.
PubMed:Comparison of the toxicities of Senecio jacobaea, Senecio vulgaris and Senecio glabellus in rats.
PubMed:Covalent binding of two pyrrolizidine alkaloids, senecionine and seneciphylline, to hepatic macromolecules and their distribution, excretion, and transfer into milk of lactating mice.
PubMed:Alkaloids from Senecio aegyptius and S. desfontainei.
PubMed:Effects of the pyrrolizidine alkaloids senecionine, retrorsine and seneciphylline on aminopyrine N-demethylase activity on the rat liver S-10 fraction.
PubMed:Hypertrophy of pulmonary arteries and arterioles with cor pulmonale in rats induced by seneciphylline, a pyrrolizidine alkaloid.
PubMed:Pyrrolizidine alkaloids: their occurrence in honey from tansy ragwort (Senecio jacobaea L.)
PubMed:Seneciphylline.
PubMed:Senecionine, Seneciphylline, Jacobine and Otosenine from Senecio cineraria.
PubMed:[Study of the solubility of platyphylline and seneciphylline alkaloids].
PubMed:[Detection of platyphylline, sarracine and seneciphylline in biological material].
PubMed:[ABOVE-GROUND PARTICLES OF SENECIO AS A SOURCE FOR OBTAINING ALKALOIDS OF PLATYPHILLINE, SARRACENINE AND SENECIPHYLLINE].
PubMed:Variation of liver function in immature fowls and susceptibility to seneciphylline.
 
Notes:
None found
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